Yellow disazo dyes.



HUG-0 GELDERMANN, OF BERLIN-GROSS-LIGHTERFELDE-OSCIT, AND FERDINAND HMS,

OF BERLIN-TREITOW, GERMANY, ASSIGNORS T0 ACTIEN GESELL$CHAFT ANILINFABRIKATION, OF BERLIN, GERMANY.

YELLOW DISAZO EYES.

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ing Grabenstrasse 1'2, Berlin-Gross-Lichterfelde-Ost, Germany, andLohmiihlenstrasse 52, Berlin-Treptow, Germany, respectively,) haveinvented certainnew and useful Improvements in Yellow Disazo Dyes, ofwhich the following is a specification.

The present invention relates to the manufacture of new dyes which dyewool yellow fast to Washing. These dyes derive from two molecules ofamino-diaryl-ether sulfonic .acids of, the benzene series and onedipyrazolone of the general formula: 1

C :N N: U icc oeg \CO-N-X--N-CO/ where X means an aromatic residue.

The dyes are in the shape of their sodium salts yellow powders easilysoluble. with a 2. To the diazo compound, obtained as described in theexample 1, a solution of 27 parts of acetoacetic ester and 33 parts ofcalcined sodium carbonate is added. The combination being complete themass is rendered weakly acid, then mixed with 32.8

parts of -4. L-dihydrazino-3.3-dimethyldiphenylmethane and; warmed for ashort time, whereby the condensation occurs. The dye is transformed intoits sodium salt and salted out. It is identical with the product of theExample 1.

The present invention is not limited to the foregoing examples or to thedetails given therein. Thus for instance isomerids,

omologues and analogues of the saidaminodiphenylether sulfonic acid maybe used w as also other dipyrazolones of other dihy drazins, theparentmaterial for the pro= duction of dipyrazolones, deriving from otherdlamms, such as tolidin,e.&-diami- Specification of Letters Patent. Patern-tad Dec. 28, 19 15. Application filed Jul 22, 1913.

Serial No. 780,564.

yellow color in Warm Water; on addition of concentrated caustic soda lyethe dye is sep arated from the aqueous solution whereas hydrochloricacid separates the free dye acid in flakes. From the orange red solutionin concentrated sulfuric acid the dye is separated on addition of. ice.By reducing the dyes yield aminodiarylether sulfonic acids besidesdiamino-derivatives of dipyrazolones.

The following examples, the parts being by weight, illustrate how thedyes may be produced:

1. One diazotizes 53 parts of the sulfonic acid made by sulfonating2amin0diphenylether, with 1% parts of sodium nitrite and 100 parts ofhydrochloric acid of 12 B. The diazo compound runs into a cooledsolution of 40 parts of the dipyrazolone derived yellow solutions fromwhich caustic sodalye separates the dye salts, whereas hydrochloric acidsepranates the free dye acids? be ing soluble in concentrated sulfuricacid to an orange-red solution. from which the dye is separated onaddition of ice; being decomposed by reduction yielding aminodiarylether sulfonic acids of the benzene series besides diaminodipyrazoloncs;the new dyes deriving from 2 molecules of aminodiarylether sulfonicacids of the benzene series and 1 molecule of a dipyrazolone of thegeneral formula:

arates the free dye acid; being soluble concentrated sulfuric acid to anorange-red solutlon irom Wh1ch the dye separates on oddltlon of 106;home; decomposed by reduction yielding Z-aniino-dlphenylether. sul fonlcecld bes 1des the dmnnno(hpyrazolone deriving from 4.4: dihydrazino 3.3dimethyldipl'lenyllnethane and ocetoocetio cster; the new dye derivingfrom 2 molecules of Z-aminodiphenylether sulfonic acid and 1 molecule ofthe dipyrazolone deriving from 4.4:dihydmzino-3.3-dimethyldiphenylmethnne and aceto-aoetic ester andcorresponding probably to the formula:

In testimony whereof We have hereunto set our hands in presence of twosubscribing Witnesses.

HUGO GELDERMANN. FERDINAND HAAS. Witnesses:

HENRY HAsPnn, VVOLDEMAR Henri

